O.J. Simpson

O.J. Simpson and his girlfriend Christina Prody at a restaurant in South Beach, Miami on September 24, 1999.

Simpson went to jail in 2008 after being convicted of armed robbery and kidnapping in a strange sports memorabilia case. Prody was arrested in 2012 and charged with stealing drugs from an elderly Minnesota couple she worked for as an in-home assistant; she was convicted and sentenced to 34 days in jail in 2013.

Photo Credit: WENN/ Manny Hernandez